(1R,2R)-1-(3'-benzyloxyphenyl)-3-(2''-methoxymethyloxy-4'',6''-dibenzyloxyphenyl)propane-1,2-diol | 863237-45-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (1R,2R)-1-(3'-benzyloxyphenyl)-3-(2''-methoxymethyloxy-4'',6''-dibenzyloxyphenyl)propane-1,2-diol
• 英文别名: (1R,2R)-3-[2-(methoxymethoxy)-4,6-bis(phenylmethoxy)phenyl]-1-(3-phenylmethoxyphenyl)propane-1,2-diol
• CAS: 863237-45-0
• 化学式: C₃₈H₃₈O₇
• 分子量: 606.716
• InChiKey: HLTHYYNLZCQJFL-FOYYQAIFSA-N

物化性质

• 熔点：
  114-116 °C
• 沸点：
  779.9±60.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.04
• 重原子数：
  45.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  86.61
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1-(3'-benzyloxyphenyl)-3-(2''-methoxymethyloxy-4'',6''-dibenzyloxyphenyl)propane-1,2-diol 在 盐酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 5.0h， 以100%的产率得到(1R,2R)-1-(3'-benzyloxyphenyl)-3-(2''-hydroxy-4'',6''-dibenzyloxyphenyl)propane-1,2-diol
  参考文献：
  名称：

  Asymmetric total synthesis of B-ring modified (−)-epicatechin gallate analogues and their modulation of β-lactam resistance in Staphylococcus aureus

  摘要：

  Two enantiomerically pure B-ring modified analogues of (-)epicatechin gallate were synthesised and their modulation of beta-lactam resistance using three strains of methicillin resistant Staphylococcus aureus (BB 568, EMRSA-15 and EMRSA-16) evaluated. Sub-inhibitory concentrations (12.5 and 25 mg/L) of the two analogues fully sensitised each of the three MRSA strains to oxacillin, reducing the MIC to less than 0.5 mg/L, identical to levels achieved with ECg. Lower concentrations demonstrated that the position and degree of hydroxylation of the B-ring is important for activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.086
• 作为产物：
  描述：

  3',4,6-tribenzyloxy-2-methoxymethyloxy-E-retrochalcone 在 sodium tetrahydroborate 、 甲基磺酰胺 、 AD-mix-β 、 溴 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三苯基膦 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 123.0h， 生成 (1R,2R)-1-(3'-benzyloxyphenyl)-3-(2''-methoxymethyloxy-4'',6''-dibenzyloxyphenyl)propane-1,2-diol
  参考文献：
  名称：

  Asymmetric total synthesis of B-ring modified (−)-epicatechin gallate analogues and their modulation of β-lactam resistance in Staphylococcus aureus

  摘要：

  Two enantiomerically pure B-ring modified analogues of (-)epicatechin gallate were synthesised and their modulation of beta-lactam resistance using three strains of methicillin resistant Staphylococcus aureus (BB 568, EMRSA-15 and EMRSA-16) evaluated. Sub-inhibitory concentrations (12.5 and 25 mg/L) of the two analogues fully sensitised each of the three MRSA strains to oxacillin, reducing the MIC to less than 0.5 mg/L, identical to levels achieved with ECg. Lower concentrations demonstrated that the position and degree of hydroxylation of the B-ring is important for activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.086